4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: 4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 120042-40-2
• Molecular Formula: C₂₀H₂₁N₅O₇
• Molecular Weight: 443.416
• Mol file: 120042-40-2.mol

Synonyms:4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Chemical Property of 4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

There total 1 articles about 4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3-Azido-3-deoxy-1,2-di-O-acetyl-5-O-(4-methylbenzoyl)-β-D-ribofuranose (75096-64-9) + thymin (65-71-4,28806-14-6,691841-57-3) → 4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (120042-40-2)

Guidance literature:

thymin; With pyridine; chloro-trimethyl-silane; Heating;

3-Azido-3-deoxy-1,2-di-O-acetyl-5-O-(4-methylbenzoyl)-β-D-ribofuranose; With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; for 5h;

DOI:10.1002/ejoc.200300177

Reference yield: 81.9%

propynoic acid ethyl ester (623-47-2) + 4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (120042-40-2) → C25H27N5O9

Guidance literature:

With dmap; In acetonitrile; at 20 ℃; for 2h; Inert atmosphere;

Reference yield:

4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (120042-40-2) → C25H29N5O8

Guidance literature:

Multi-step reaction with 3 steps

1: dmap / acetonitrile / 2 h / 20 °C / Inert atmosphere

2: water; ammonium hydroxide / methanol / 1.5 h / 0 °C

3: silver(l) oxide / 5 h / 50 °C

With dmap; ammonium hydroxide; water; silver(l) oxide; In methanol; acetonitrile;

upstream raw materials:

3-Azido-3-deoxy-1,2-di-O-acetyl-5-O-(4-methylbenzoyl)-β-D-ribofuranose

thymin

Downstream raw materials:

1-(3'-azido-3'-deoxy-β-D-ribofuranosyl)thymine

1-(3-azido-2-fluoro-2,3-dideoxy-β-D-ribofuranosyl)thymine

1-(3-azido-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine

1-(3-azido-2,3-dideoxy-2-fluoro-5-O-trityl-β-D-ribofuranosyl)thymine